Process for the preparation of sulphonyl isocyanide dichlorides



United States Patent 3,299,134 PROCESSFOR THE PREPARATIUN 0F SUL- PHONYL ISOCYANIDE DICHLORIDES Bertram Anders, Cologne-Stammheim, Engelbert Kiilrle,

Bergisch-Gladbach, and Karlfried Dickor, Leverkrisen, Germany, assignors to Far-benfabriken Bayer Aktiengesellschaft, Leverkusen, Germany, a German corporation N0 Drawing. Filed Nov. 19, 1964, Ser. No. 412,309 Claims priority, application Germany, Dec. 11, 1963,

5 Claims. (Cl. 26 0-556) It has now been found that sulphonyl isocyanidedichlorides may be obtained by reacting salts of sulphonyliminodithiocarbonic-acid or sulphonyl-isothiocyanates with chlorine or sulphuryl chloride :at temperatures of to +100 C. if desired in an inert solvent.

As starting compounds for the process of the invention sulphonyliminodithiocarbonic-acid salts of the general formula may be used, wherein R denotes an alkyl-, cycloalkylor aryl radical which may be substituted by halogen-, nitro-, alkyl-, arylor trifiuoromethyl groups of the radical and M denotes alkali-metal or ammonium ions and R and R separately represents lower alkyl radicals or may, together with the nitrogen atom, denote a heterocyclic ring which may also contain oxygen, sulphur or other hetero-atoms. These compounds may be prepared for example, from sulfonamides, carbon disulphide and an alkali metal hydroxide according to Angewandte Chemie 74 (1962) 753.

Alternatively, according to an earlier proposal of the applicants, these sulphonyli-minodithiocarbonic acid salts may first be reacted with acid halides at temperatures of 10 to +120 C., if desired in a solvent, to form the corresponding sulphonyl is-othiocyanatesof the general formula These RSO N=CCI wherein R has the meaning already given above.

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The following may, for example, be used as inert solvents:

Chlorinated hydrocarbons such as carbon tetrachloride, chloroform or chlo-robenzene.

The process of the invention may be carried out at temperatures between 10 and C., preferably between 0 and 50 C. For example, suspensions of sulphonyliminodithiocarbonioacid salts or solutions of the isothiocyanates may be treated in one of the above mentioned solvents with chlorine or sulphuryl cholride. When isothiocyanates are used, the reaction may be carried out without the use of solvents. The reaction mixture may in general be worked up by distillation. The sulphonyl isocya-nide dichlorides then remain behind as oily liquids or solid residues.

The compounds obtainable according to the invention are new and may be used as intermediate products or as agents against pests, such as insects, for instance Plulella maculipennis, Drosophila melanogasler and Myzus persicae, and mites, for instance Tetranychus urticae.

The following compounds for example exhibit the indicated killing rates in percent, when used in the form of powders containing 5% of active ingredient in an amount of 40 kg/ha:

Drosophila melanogasicr killing rate after 24 hours oH3-s02-N=ccn CH3SO2N=CClz 100 C1 SOzN=CClg 100 Example 1 57 g of Cl 2 are passed into 75 g of benzenesulphonyliscthiocyanate at 60 C. no solvent being added. The low boiling constituents are then removed by distillation in vacuo, benzene suphonylisocyanide-dichloride 122 C., 0.1 mm. Hg.

Example 2 60 g. of C1 are passed into a suspension of 93 g. of benzene-suplhonyliminodithiocarbonic-acid -dipotassium salt in 500 cc. of CCL; at 1520 C. The salt is then removed by filtration and the filtrate is freed from solvent. Benzenesulphonylisocyanide-dichloride of B.P. 122-125 C., 0.1 mm. Hg is obtained as residue.

Example 3 By an analogous method, the following sulphonylisocyanide dichlorides are obtained:

Oily.

B1. 0.1 mm. Ilg.,

ALP. 78 C.

ALP. 87 C.

M.P. 64 C.

4 We claim: 1. A sulphonyl isocyanide dichloride of the formula References Cited by the Examiner FOREIGN PATENTS 5/1962 Great Britain. 10/ 1962 Great Britain.

OTHER REFERENCES Bcilsteins Handbuch der Organischen Chemie, volume 11, 4th ed., pages 43 and 86, Verlag Von Julius Springer, Berlin, Germany (1928).

JOHN D. RANDOLPH, Primary Examiner. 

1. A SULPHONYL ISOCYANIDE DICHLORIDE OF THE FORMULA
 2. BENZENESULPHONYLISOCYANIDE DICHLORIDE. 